1,1'-Carbonyldiimidazole → HCID 10091375, compound

HRID 1708402Notes

Reaction equation

HRID 1708402 reaction equation
[CH2:1]([C:4]1[N:9]=[C:8]([CH3:10])[N:7]=[C:6]([NH:11][NH2:12])[C:5]=1[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]#[N:27])=[CH:16][CH:15]=1)[CH2:2][CH3:3].[C:28](N1C=CN=C1)(N1C=CN=C1)=[O:29]>O1CCCC1>[CH2:1]([C:4]1[N:9]=[C:8]([CH3:10])[N:7]2[C:28](=[O:29])[NH:12][N:11]=[C:6]2[C:5]=1[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]#[N:27])=[CH:16][CH:15]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 10473537HCID 10473537, compound

Product 1

HCID 10091375HCID 10091375, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

33.4 g of 6-n-propyl-2-methyl-4-hydrazino-5-[(2'-cyano-4-biphenylyl)methyl]pyrimidine, prepared in Example 12, are dissolved in 600 ml of tetrahydrofuran. 15.2 g of carbonyldiimidazole are added and the mixture is heated to reflux for 1 h 30 min. The solvent is evaporated off under vacuum and the residue is taken up with water and then extracted with chloroform. The organic phase is dried over magnesium sulphate and evaporated under vacuum; the residue obtained crystallises in an ether/ethyl acetate mixture to give 26.4 g of 7-n-propyl-5-methyl-8-[(2'-cyano-4-biphenylyl)methyl]-1,2,4-triazolo-[4,3-c]pyrimidin-3(2H)-one in the form of crystals of melting point 196° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 1 h 30 min
  3. customThe solvent is evaporated off under vacuum
  4. extractionextracted with chloroform
  5. dry with materialThe organic phase is dried over magnesium sulphate
  6. customevaporated under vacuum
  7. customthe residue obtained
  8. customcrystallises in an ether/ethyl acetate mixture

Sources & evidence

ORD record
ord-2f06ac78cf254e77b4988f149577fcc8
Source dataset
uspto-grants-1994_10
Patent number
US05358950

Reaction notes

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